(a) Interpretation: The following pericyclic reaction is to be classified. (More than one classification is possible.) Concept introduction: Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

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Answer 1

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Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.

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(a) Name the reactant (including E/Z configuration) and draw the structure of the major product for the following reaction. + HBr (b) Explain your answer for the product in part (a), and include the structure of the carbocation intermediate in your explanation. (c) Draw the mechanism for the reaction in part (a), showing all intermediates and electron movement with arrows.

For each of the following, write the major product(s) and then draw out each step in the mechanism using curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show explicitly ALL bonds being broken or formed. Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of electrophile involved in the nucleophilic attack. MO diagrams are not necessary. (a). (b). -CHO 2. H₂O 1. LiAlH4 2. H₂O MgBr , ether

(b) Distinguish each as aromatic or antiaromatic in terms of electronic basis. Explain which one is more stable. (i) Compound A Compound B (ii) Compound C Compound D (iii) Compound E Compound F

Answer 2

Question

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.

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Answer 3

Question

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.

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Answer 4

Question

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.

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Answer 5

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.

Answer 6

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Answer 7

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 28 - Prob. 28.1P Ch. 28 - Prob. 28.2P Ch. 28 - Prob. 28.3P Ch. 28 - Prob. 28.4P Ch. 28 - Prob. 28.5P Ch. 28 - Prob. 28.6P Ch. 28 - Prob. 28.7P Ch. 28 - Prob. 28.8P Ch. 28 - Prob. 28.9P Ch. 28 - Prob. 28.10P

Solution Summary: The author explains that the pericyclic reaction can be classified as an uncatalyzed intramolecular reaction.

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